Hydrochloric Acid → Ethyl (2-hydroxy-2,3-dihydro-1H-inden-2-yl)acetate

HRID 1731146Notes

Reaction equation

HRID 1731146 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].Cl>[Zn].C1C=CC=CC=1>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][C:2]1([OH:10])[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetate2×HCID 119832-Indanone

Product 1

HCID 54446307Ethyl (2-hydroxy-2,3-dihydro-1H-inden-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-indanone (13.2 g), ethyl bromoacetate (16.7 g), benzene (150 ml) and purified zinc (6.5 g) is stirred and heated at 50° C. Iodine (0.5 g) is added to catalyze the reaction. A rather vigorous reaction sets in after about 30 min. and the heating is discontinued. After the mixture ceases boiling, 4 g of fresh zinc and 10 g of ethyl bromoacetate is added, the reaction mixture is heated at reflux for 2 hr. and allowed to stand overnight at room temperature. The zinc addition-compound is decomposed by adding 200 ml of cold 10% hydrochloric acid. The aqueous layer is separated, extracted twice with benzene, all organic extracts are combined and dried (MgSO4). The filtrate is concentrated and the residue distilled under reduced pressure yielding 2-hydroxyindane-2-acetic acid ethyl ester, bp. 163°-166° C/10 mm.

Workup

  1. custompurified zinc (6.5 g)
  2. additionIodine (0.5 g) is added
  3. customthe reaction
  4. customA rather vigorous reaction sets in after about 30 min.
  5. temperaturethe reaction mixture is heated
  6. temperatureat reflux for 2 hr
  7. customThe aqueous layer is separated
  8. extractionextracted twice with benzene
  9. dry with materialdried (MgSO4)
  10. concentrationThe filtrate is concentrated
  11. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-281f3c00d16947deb590985a8d013a80
Source dataset
uspto-grants-1976_11
Patent number
US03995052

Reaction notes

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